Dialkynylpyrenes: strongly fluorescent, environment-sensitive DNA building blocks.
Two isomeric dialkynylpyrene phosphoramidites and their incorporation into oligonucleotides are described. The pyrene units closely resemble the well-known perylene bisimide dye PDI with regard to the ability to self-organize within a DNA duplex. In addition, dialkynylpyrenes exhibit significant monomer and remarkably strong excimer fluorescence. The dialkynylpyrene building blocks are promising candidates for applications in diagnostic tools, such as excimer-based molecular beacons, as well as for novel DNA-based materials with special optical properties.
Bittermann
Holger
H
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, Bern, CH-3012, Switzerland.
Siegemund
Doreen
D
Malinovskii
Vladimir L
VL
Häner
Robert
R
D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure; D063088:Phosphoramides; D010756:Phosphoric Acids / Q000737:chemistry; D011721:Pyrenes / Q000737:chemistry*; D013053:Spectrophotometry; D013379:Substrate Specificity; D013696:Temperature
D000480:Alkynes; D000577:Amides; D005456:Fluorescent Dyes; D063088:Phosphoramides; D010756:Phosphoric Acids; D011721:Pyrenes; C005438:phosphoramide; D004247:DNA